Ethanol → 5-(4-Aminophenyl)thieno[2,3-d]pyrimidin-4-amine

HRID 227609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 227609
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]3[C:17]([NH2:19])=[N:16][CH:15]=[N:14][C:13]=3[S:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.C(O)C>C1COCC1.O.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:18]3[C:17]([NH2:19])=[N:16][CH:15]=[N:14][C:13]=3[S:12][CH:11]=2)=[CH:8][CH:9]=1

Komponenten

6

Edukt 2

HCID 702EthanolHCID 597942485-(4-Nitrophenyl)thieno[2,3-d]pyrimidin-4-amine

Produkt 1

HCID 250237745-(4-Aminophenyl)thieno[2,3-d]pyrimidin-4-amineAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A suspension of Example 58C (0.5 g, 1.83 mmol) in THF (30 mL), water (15 mL), and ethanol (40 mL) was heated to 50° C., treated with iron powder (0.616 g, 11.02 mmol), heated to between 70 and 80° C. for two hours, and filtered while hot through diatomaceous earth (Celite®). The pad was washed with TBF (10 mL) and ethanol and the combined filtrates were concentrated. The residue was partitioned between water and ethyl acetate and the aqueous phase was extracted three times with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated to give 0.432 g of the desired product. MS (CI) m/e 243 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 8.30 (s, 1H); 7.28 (s, 1H); 7.11 (d, J=8.4 Hz, 2H); 6.68 (d, J=8.4 Hz, 2H); 5.39 (br s, 2H).

Aufarbeitung

  1. temperatureheated to between 70 and 80° C. for two hours
  2. filtrationfiltered while hot through diatomaceous earth (Celite®)
  3. washThe pad was washed with TBF (10 mL) and ethanol
  4. concentrationthe combined filtrates were concentrated
  5. customThe residue was partitioned between water and ethyl acetate
  6. extractionthe aqueous phase was extracted three times with ethyl acetate
  7. washThe combined extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f23060ba9910479984dc57b40ae9d09e
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560552B2

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